Southfield Vacation Rentals

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Vacation Rentals in Southfield

A labour of love in the south of the island
Pool
A labour of love in the south of the island
The price is $286
$395 total
includes taxes & fees
Jun 21 - Jun 22
A labour of love in the south of the island
Mountain Top Villa
Outdoor pool
Mountain Top Villa
3.5 star property
8.6 out of 10, Excellent, (20)
"We enjoyed our stay at the villa, we stayed there for our honey moon, they even helped us take some really nice pics after our wedding"
The price is $62
$97 total
includes taxes & fees
Jun 21 - Jun 22
Mountain Top Villa
Turtles Nest Villa
Land view from property
Turtles Nest Villa
4.0 star property
9.6 out of 10, Exceptional, (8)
"Sugar & Spice make Turtles Nest feel like home. We loved the pool and being able to eat breakfast outside each morning. It was very helpful to have bathrooms inside each room as a family of 5 being able to come in and shower quickly to make it back out to our next stop. The homemade breakfast each morning was amazing. Peta-Gay, Vincent and Zeb are very kind and thoughtful. Our cleaner lady who came was a Godsend who helped when my baby got sick. Next time we are in this area we will for sure...
Turtles Nest Villa
The Hideaway cozy , centrally located apartment 3 minutes from town center
Fridge, microwave, oven, stovetop
The Hideaway cozy , centrally located apartment 3 minutes from town center
10.0 out of 10, Exceptional, (2)
"Very clean and comfortable accommodation. Safe and quiet area. The host was amazing, very understanding and responded to guests in a timely manner. I would definitely recommend to anyone. You will not be disappointed! Thanks Carla "
The price is $80
$112 total
includes taxes & fees
Jun 24 - Jun 25
The Hideaway cozy , centrally located apartment 3 minutes from town center
NEW LISTING!! Seaside Villa -1 minute walk to beach - DISCOUNT AVAILABLE!!
Beach nearby, sun loungers, beach towels
NEW LISTING!! Seaside Villa -1 minute walk to beach - DISCOUNT AVAILABLE!!
10.0 out of 10, Exceptional, (3)
"Wonderful villa with a great host and onsite staff. Walk to a quiet, beautiful beach. Plenty of room. All rooms have en-suite bathrooms! Big plus for a big crew! We had the chefs prepare two meals and both were extraordinary! Full kitchen to prepare other meals. Five star visit!"
NEW LISTING!! Seaside Villa -1 minute walk to beach - DISCOUNT AVAILABLE!!
Oceanfront Luxury Villa: Private Beach & Staff
Exterior
Oceanfront Luxury Villa: Private Beach & Staff
9.8 out of 10, Exceptional, (31)
"The house was a great place to wake up every morning. The views, the private beach and the pool were all great. We spent our nights on the beach side veranda looking directly at a perfect sunset. The house was clean, area is safe and would stay again. The owner was responsive and easy to coordinate with. Shane the property manager is a good guy, easy to work with, great cook and very help full. Thanks for the make the stay with my dad and friend memorable trip."
Oceanfront Luxury Villa: Private Beach & Staff
Luxurious Beach Front Villa with Pool - Out of the Blue Villa
Indoor pool
Luxurious Beach Front Villa with Pool - Out of the Blue Villa
10.0 out of 10, Exceptional, (73)
"I loved everything about this home. The other reviews speak about all of the positives, so I’m not going to rehash those. Just know that the beach is great. The pool is great. The rooms are great. The staff is wonderful. The food was phenomenal. It was one of the most relaxing stays that I have ever had. If you want some negatives, I’ll give you two - there were a lot of bugs (welcome to a tropical island) and the road to get there was pretty trash (welcome to Jamaica). These were really minor...
Luxurious Beach Front Villa with Pool - Out of the Blue Villa
Zero minutes to the most prestigous cove in the area
On the beach, beach towels
Zero minutes to the most prestigous cove in the area
9.4 out of 10, Exceptional, (34)
"We stayed at Villa Optima for 22 nights. The host Paolo was wonderful. He responded essentially immediately, and provided extra items for the house whenever we asked. He helped us buy fresh fish and rum and other things we needed. The private pool was very pleasant, and has some nice shaded areas so you can hang out there for a long time. The beach was just 50 yards away. It is a sandy beach and you can easily swim in the ocean. Usually there was no-one else on the beach, it was never crowded....
The price is $300
$438 total
includes taxes & fees
Jun 23 - Jun 24
Zero minutes to the most prestigous cove in the area
Sweet Escape ~the villa "Your Island Utopia" The Sweetest Escape
Outdoor pool
Sweet Escape ~the villa "Your Island Utopia" The Sweetest Escape
9.8 out of 10, Exceptional, (28)
"We really enjoyed our week at Sweet Escape. The house was clean and spacious, beds were comfortable, and we loved the outdoor areas (pool, pergola, beach bed, and beach). Mark was absolutely fantastic! He made us delicious dinners and hearty breakfasts to start our day. We took care of the shopping, but he guided us at the grocery store and made recommendations. There were plenty of fun activities to do within a reasonable driving distance of the house (Black River Safari (5 min), Appleton Rum...
Sweet Escape ~the villa "Your Island Utopia" The Sweetest Escape
Tranquil Beachfront Oasis ~ Pool ~ Boat Tour
Living area | Smart TV, books, stereo
Tranquil Beachfront Oasis ~ Pool ~ Boat Tour
9.8 out of 10, Exceptional, (7)
"A bit of off the beaten path paradise was just what we needed and just what we got! Everyone was kind, responsive, and helpful. Very refreshing! Thanks everyone!"
Tranquil Beachfront Oasis ~ Pool ~ Boat Tour
Villa Serene Jewel of Black River 4 bedroom 5bathrooms
Terrace/patio
Villa Serene Jewel of Black River 4 bedroom 5bathrooms
9.6 out of 10, Exceptional, (11)
"The pictures do not give this Villa justice, it is beautiful! We had an amazing time there! We were looking for rest and relaxation and that is exactly what we got!! Shamoir the cook was incredible! Sheryl was quick to respond to any questions we had! We will definitely go back!"
Villa Serene Jewel of Black River 4 bedroom 5bathrooms
"Main House at Shakespeare Cottage"
Beach
"Main House at Shakespeare Cottage"
9.4 out of 10, Exceptional, (3)
"A large group of us Peace Corps workers stayed there for a weekend and LOVED it. It is perfect for a large group. The communication was great and the staff is very nice. The local contact, Vaughn, could not have been more helpful and friendly. We will definitely be going back! "
The price is $180
$180 total
includes taxes & fees
Jun 22 - Jun 23
"Main House at Shakespeare Cottage"
Deano's Cottages
Lake
Deano's Cottages
4.5 star property
7.0 out of 10, Good, (4)
"Very nice and comfortable "
The price is $58
$68 total
includes taxes & fees
Jul 4 - Jul 5
Deano's Cottages
Bramble Beach Villa -Main House 3 Bedroom Modern Luxury 2 minutes walk to beach
A rooftop pool
Bramble Beach Villa -Main House 3 Bedroom Modern Luxury 2 minutes walk to beach
10.0 out of 10, Exceptional, (1)
"This place has everything you need! The staff, 2 pools, 2 minute walk to the beach, game room, trampoline, pickleball court, basketball court, games, the mountain views, ocean view, and all the wonderful people you meet along the way. We will definitely be back. Thank you everyone for making our trip so incredibly special."
Bramble Beach Villa -Main House 3 Bedroom Modern Luxury 2 minutes walk to beach
VillaMerissa Nestled between two unspoiled beaches Pool/JackSprat/WiFi/Gym/Staff
Beach nearby, beach towels
VillaMerissa Nestled between two unspoiled beaches Pool/JackSprat/WiFi/Gym/Staff
10.0 out of 10, Exceptional, (4)
"Relaxing due to the villa was away from the tourists. Great scenery going through the mountains and down to valley and seaside It was awesome"
VillaMerissa Nestled between two unspoiled beaches Pool/JackSprat/WiFi/Gym/Staff
Unforgettable Villa: Jamaica's Rare Private Escape
Property grounds
Unforgettable Villa: Jamaica's Rare Private Escape
Unforgettable Villa: Jamaica's Rare Private Escape
Coral Bay Chateau - Luxury Villa in Treasure Beach
Property grounds
Coral Bay Chateau - Luxury Villa in Treasure Beach
10.0 out of 10, Exceptional, (1)
"My husband’s 60 birthday bash with my family and friends! The Chateau is very spacious and comfortable. We were 14 adults and every couple had their own room and bathroom. The house has a wonderful outdoor space with a beautiful view and pool and many shaded areas! The staff is wonderful! The chefs made us some amazing breakfasts and dinners Jamaican style! Amazing! The beach was beautiful. We swam every day. It is a 10 minute walk. We chose the house because of the view and it didn’t...
Coral Bay Chateau - Luxury Villa in Treasure Beach
Mckay's Private Appartment
Private kitchen
Mckay's Private Appartment
9.0 out of 10, Wonderful, (2)
"Property was amazing to stay, very private and inviting."
The price is $45
$72 total
includes taxes & fees
Jun 21 - Jun 22
Mckay's Private Appartment
Cashaw Cabin - Private A-frame Cabin With Pool
Villa, 1 Bedroom, Smoking, Private Pool | Exterior
Cashaw Cabin - Private A-frame Cabin With Pool
2.0 star property
The price is $110
$128 total
includes taxes & fees
Jul 16 - Jul 17
Cashaw Cabin - Private A-frame Cabin With Pool
Bramble Beach Villa
Rooftop terrace
Bramble Beach Villa
3.0 star property
10.0 out of 10, Exceptional, (1)
Bramble Beach Villa
Don't see what you're looking for?
See all available properties in Southfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Southfield Vacation Rental Travel Info

Number of vacation rentals
20
Known landmarks
Lovers Leap, Billy Bay Beach and Callabash Bay Beach
International airport
Montego Bay (MBJ-Sir Donald Sangster Intl.)

Other types of properties in Southfield you may be interested in

Sea Coast Inn & Suites
Reception
Sea Coast Inn & Suites
3.0 star property
7.2 out of 10, Good, (11)
"The host was amazing and chef made some great breakfast also very positive employee and great morning view "
The price is $99
$123 total
includes taxes & fees
Jun 21 - Jun 22
Sea Coast Inn & Suites
A labour of love in the south of the island
Pool
A labour of love in the south of the island
The price is $286
$395 total
includes taxes & fees
Jun 21 - Jun 22
A labour of love in the south of the island
Jakes
Beach bar
Jakes
3.5 star property
9.2 out of 10, Wonderful, (265)
"Beautiful place "
The price is $150
$181 total
includes taxes & fees
Jun 21 - Jun 22
Jakes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Southfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $45 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southfield rentals

At Expedia, we put the best Southfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Southfield?

Yes, we offer vacation rentals close to popular attractions in Southfield, or you can select a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Southfield has to offer?

"Main House at Shakespeare Cottage": This vacation home rental near Southfield is located on a river and has a balcony, a garden, and free WiFi to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the spa tub in this rental home to help you unwind.

What can I see and do in Southfield?

While you're exploring the area, Jamaica Beaches and Calabash Bay are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Lovers Leap and Billy Bay Beach.

What are vacation rentals like in Southfield?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Southfield. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for families.

Recent reviews of Southfield properties
Expedia verified reviews

Jakes

Jakes

5/5 Excellent
"Beautiful place "
A verified traveler stayed at Jakes
Posted 2 days ago
Jakes